The Hilbert-Johnson Reaction of 2,4-Dialkoxypyrimidines with Halogenoses

Add time:07/31/2019    Source:sciencedirect.com

Publisher SummaryThis chapter discusses the reaction of 2, 4-Dialkoxypyrimidines with Halogenoses. The reaction of a 2, 4-dialkoxypyrimidine with a halogenose or an alkyl halide has been assumed to proceed via a quaternary salt as intermediate. Thus, the stable l-methyl-2-methoxy-4-aminopyrimidinium iodide has been obtained from 2-methoxy- 4-aminopyrimidine and methyl iodide. Treatment of the quaternary salt with aqueous silver sulfate yielded 1-methylcytosine. Under the conditions of the reaction, the 2, 4-dialkoxypyrimidines can furnish the following by-products: uracil, 1-alkyluracil, 3-dialkyluracil, 4-alkoxy-2(lH)-pyrimidinone, and l-alkyl-4-alkoxy-2(lH)-pyrimidinone.

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